Wind tunnel experiments were performed to examine the effect of a tall tower on the flow around an otherwise uniform array of buildings. Additionally, preliminary CFD simulations were run to visualize the flow with more resolution. The model used in both the wind tunnel and CFD studies was designed to simulate an area of Brooklyn, NY, USA, where blocks of residential row houses form a neighborhood bordering a major urban highway. This area was the site of a field study that, along with the work reported here, had the goal of improving the understanding of airflow and dispersion patterns within urban microenvironments. Results reveal that a tall tower has a dramatic effect on the flow in the street canyons in the neighboring blocks, enhancing the exchange between the street canyon flow and the freestream flow aloft. In particular, vertical motion down the windward side and up the leeward side of the tower resulted in strong flows in the lateral street canyons and increased winds in the street canyons in the immediate vicinity of the tower. These phenomena were visible in both the wind tunnel and CFD results, although some minor differences in the flow fields were noted.